Maleic anhydride derivatives as catalysts for N -oxidation of pyridine using hydrogen peroxide

Maleic anhydride derivatives were evaluated as catalysts in -oxidation of various pyridine substrates using hydrogen peroxide (H O ). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In c...

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Published inRSC advances Vol. 14; no. 43; pp. 31657 - 31662
Main Authors Gajeles, Ghellyn, Lee, Kyung-Koo, Lee, Sang Hee
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 01.10.2024
The Royal Society of Chemistry
Subjects
Catalysts
Chemistry
Dicarboxylic anhydride
Hydrogen peroxide
Maleic anhydride
Oxidation
Oxidizing agents
Peracids
Pyridines
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Abstract Maleic anhydride derivatives were evaluated as catalysts in -oxidation of various pyridine substrates using hydrogen peroxide (H O ). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid-anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H O has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.
AbstractList Maleic anhydride derivatives were evaluated as catalysts in N-oxidation of various pyridine substrates using hydrogen peroxide (H2O2). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid–anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H2O2 has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.
Maleic anhydride derivatives were evaluated as catalysts in N -oxidation of various pyridine substrates using hydrogen peroxide (H 2 O 2 ). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid–anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H 2 O 2 has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.
Maleic anhydride derivatives were evaluated as catalysts in N -oxidation of various pyridine substrates using hydrogen peroxide (H 2 O 2 ). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid–anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H 2 O 2 has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates. The anhydride–diacid equilibrium is crucial for the catalytic cycle of maleic anhydride derivatives in N -oxidation of pyridine derivatives with H 2 O 2 . This catalytic system can replace stoichiometric peracids, such as m -CPBA, as oxidants.
Maleic anhydride derivatives were evaluated as catalysts in -oxidation of various pyridine substrates using hydrogen peroxide (H O ). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid-anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H O has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.
Maleic anhydride derivatives were evaluated as catalysts in N-oxidation of various pyridine substrates using hydrogen peroxide (H2O2). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid-anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H2O2 has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.Maleic anhydride derivatives were evaluated as catalysts in N-oxidation of various pyridine substrates using hydrogen peroxide (H2O2). Depending on the electronic properties of the pyridine substrates, pyridines with electron-donating groups reacted well with 2,3-dimethylmaleic anhydride (DMMA). In contrast, 1-cyclohexene-1, 2-dicarboxylic anhydride (CHMA) was most effective for electron-deficient pyridines. The different performance of these two anhydrides is attributed to the diacid-anhydride equilibrium, which is crucial for regenerating the peracid oxidant through an anhydride intermediate in the catalytic cycle. This approach using a catalytic amount of anhydride with H2O2 has the potential to replace stoichiometric amounts of percarboxylic acid as an oxidant for a broader range of organic substrates.
Author Lee, Kyung-Koo
Lee, Sang Hee
Gajeles, Ghellyn
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Physical Science Department, West Visayas State University, Luna St., La Paz, Iloilo City, 5000 Iloilo, Philippines is the authors present address.
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Snippet Maleic anhydride derivatives were evaluated as catalysts in -oxidation of various pyridine substrates using hydrogen peroxide (H O ). Depending on the...
Maleic anhydride derivatives were evaluated as catalysts in N -oxidation of various pyridine substrates using hydrogen peroxide (H 2 O 2 ). Depending on the...
Maleic anhydride derivatives were evaluated as catalysts in N-oxidation of various pyridine substrates using hydrogen peroxide (H2O2). Depending on the...
Maleic anhydride derivatives were evaluated as catalysts in N -oxidation of various pyridine substrates using hydrogen peroxide (H 2 O 2 ). Depending on the...
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Index Database
StartPage 31657
SubjectTerms Catalysts
Chemistry
Dicarboxylic anhydride
Hydrogen peroxide
Maleic anhydride
Oxidation
Oxidizing agents
Peracids
Pyridines
Title Maleic anhydride derivatives as catalysts for N -oxidation of pyridine using hydrogen peroxide
URI https://www.ncbi.nlm.nih.gov/pubmed/39376527
https://www.proquest.com/docview/3117043439
https://www.proquest.com/docview/3114152963/abstract/
https://pubmed.ncbi.nlm.nih.gov/PMC11456919
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